This chapter examines the playful design and enactment of games for learning, and details generative and provocative attributes of playful multistakeholder partnerships for information and communications technology- supported game-based learning in international contexts. Drawing upon the experiences of two educational technology research and design groups, the chapter first identifies four design principles that have guided various global - and playful - game-based learning partnerships in Jamaica, Oman, South Africa, and Switzerland. Such international partnerships were designed as opportunities to co-construct game-based learning by articulating the permitted, establishing collaborative presence, attending carefully to trust, and fostering third space. The second half of this chapter features a case study of ICT-supported game-based learning in Oman, and describes different ways in which a playful multistakeholder partnership can be enacted in a cross-cultural setting. The subject of this case study is Place Out Of Time (POOT), a trans-historical simulation of a trial in which students play guests who come from a range of places and time throughout history to discuss some of the great issues of humankind, and to bring the wisdom of history to a modern-day problem. Utilizing narrative methods, four vignettes from playing POOT in Oman are presented that convey the complex, and sometimes contradictory characteristics of playful partnerships for game-based learning in a developing region. The chapter concludes by arguing for a more critical playfulness in game-based learning that can support all partners and players in confronting biases, celebrating difference, and creatively addressing local and global needs.